


Whiskey and Sinners

by bouncydean, cptsdgavino (orphan_account)



Category: Supernatural
Genre: AU, Alternate Universe - 20s, Humor, I don't know what to tag this as, M/M, Roaring Twenties, help I'm so confused
Language: English
Status: In-Progress
Published: 2013-11-30
Updated: 2014-02-23
Packaged: 2018-01-03 02:05:22
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 11,964
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1064409
Author URL: https://archiveofourown.org/users/bouncydean/pseuds/bouncydean, https://archiveofourown.org/users/orphan_account/pseuds/cptsdgavino
Summary: <blockquote class="userstuff">
              <p>Dean Winchester is in a shitload of trouble. After losing his job, the threat of moving onto the snowy streets of Detroit becomes very real. So he does the only logical thing to do in 1928; join the infamous Angellotte Gang of Detroit's downtown. Spending his days as a Rum Runner, Dean meets the oh-so-very-kissable Castiel Novak and his world is turned upside-down again and again.</p>
            </blockquote>





	1. The Second Worst Day of Dean Winchester's Life

**Author's Note:**

> Multichapter fic??? Wowie! Better not abandon this one. I'm super excited! Anyway. I'd like to thank my co-writer Maddy who will start her writing soon-ish and my lovely beta Riley who took time out of her busy life (laugh track plays in the distance) to cater to my little needs. Okay I hope you like!

The second worst day of Dean Winchester's life happened to fall on a Thursday in January (right at the beginning of 1928, the best year of his life). Doesn't make much sense, but that’s Dean for you.

"DEAN WINCHESTER!"

The man cringed at the sound of the shrill voice ringing out through the Detroit garage in which he worked. He sure didn't recognize the voice, but anyone yelling his name that loud is either in bed with him or about to put him in the dirt (two guesses which).

"You! You're Dean Winchester?"

Dean turned around to see a very pretty and very angry flapper storming past Model T's in his direction.

"Maybe," he smiled and wiped his hands, "Who wants to know?"

Dean never got an answer because next thing he knew the woman slapped him so hard he was seeing spots.

"You slept with my husband!" she shouted.

"Pardon me?"

"Don't play coy, you slept with my husband, Victor Rodgers! Don't deny it! He said so."

"Baloney!"

"You scoundrel! You fucked my husband!"

"Ma'am!" a gruff voice shouted from somewhere behind Dean. "Watch your fucking language!"

Rufus Turner, the garage's manager is a tall, rugged man who has a look about him that he's seen a lot of shit. He’s just the guy Dean needs to get rid of this girl before the unthinkable happens.

"What's with all the yelling?" Rufus asked as he walked up behind Dean.

"This dame is accusing me of necking her husband!" Dean exclaimed.

"Well did 'ya?"

Before his smirk could be noticed he replied maybe too quickly, "Of course not!"

The dame across from him scoffed and muttered, "I saw the hickeys." earning Dean a judgemental glare from Rufus.

"I didn't, okay! I have a girlfriend!" Dean defended.

"Mister Turner," the dame piped up again, "I’m an extremely reasonable woman. I’m very modern, you know. I either want this man fired, or burned at the stake. Your choice."

"I'm not firing my best worker."

She laughed harshly. "Then I'll have both of you fired and this place shut down." Then, quieter, "I have connections. I'll get you both bumped off."

Dean swallowed thickly and Rufus took a step back. Ever since the Prohibition anyone with any gang connections rose above everyone else. Dean didn't know what kind of bimbo would want to associate with this dumb dora, but facing possible murder he knew it was over.

"Dean..." Rufus said quietly, "I don't want to fire you. But if you’re a homosexual, I suggest you walk out that door right now."

Dean took a shaky breath and closed his eyes. He either walks out that door now and leaves behind rumors, or he stays, gets fired, and risks never getting a good job again. Opening his eyes again he glared daggers at the woman.

"For your information, I swing both ways." he turned on his heel towards the door, barely stopping to grab his bag on the way by.

He was so screwed.

_____~•~____

Walking through the cold streets of Detroit's downtown, his hands shoved deep into the pockets of his overcoat, Dean was forced to retreat into his own head.

He wondered what kind of rumors he would leave behind back at the garage. He wondered how Rufus would look at him if he passed him by in the street. He wondered how he would feed his brother Sam, now, what would happen to them if they had to move back onto the streets, how he could hide the reasoning of his firing from Lisa.

Dean and Lisa had been together for a year and a half now. Their relationship had been stable until last week when Dean started some stupid spat about money, he honestly doesn't remember. But that was the night he decided to throw it back in Lisa's face by sleeping with Victor.

Truth be told, it wasn't very hard for Dean to pick up the first sap that caught his eye. For a man of 22, he was a looker. Thickly lashed green eyes, freckles everywhere, and a dark enough past to send Al Capone crawling back to his mother. He was ideal for a one-nighter for guys and girls alike.

Dean supposed he always swung both ways. It wasn't a big deal for him until his first kiss with another man had gotten a bottle smashed over his head by an onlooker. Before then, poor boy thought it was normal.

Now however, he knew he was anything but normal, and he accepted that, whether or not anyone else did. Kicking the snow at his feet, he shook off the thoughts he'd rather not think about at the moment and occupied the time counting the cracks in the sidewalk as he walked.

Dean reached the shop where his apartment rested above just as he registered his feet starting to go numb from the cold. However, instead of going in the front door through the smoke shop, Dean decided he'd rather not talk to Bobby at the moment and walked the several extra feet around the back.

"Sammy, I'm back! You home?" Dean shouted as he threw open the apartment door.

"Yeah, Dean," came his brother's sarcasm-riddled reply, "S'not like I was sleeping or anything! Come right in!"

"Why are you sleeping?" Dean slammed the door extra loud to annoy Sam, "It's 3:00!" He elaborated.

Emerging from the hallway in pajama pants and a too-big shirt (which Dean didn't was possible considering the size of his not-so-little brother) came a very grumpy-looking Sam.

"In case it slipped your mind," Sam yawned, "I had a late night last night because my ass of an older brother decided it was a good idea to have sorry-I'm-such-an-idiot-sex at four this morning."

"Speaking of which, where is Lisa?" Dean questioned looking around his giant of a brother into the bare apartment.

"She and Jess decided to spend your money and go dress shopping" Sam replied, scratching his stomach.

At that, Dean felt his usual demeanor falter and he hoped to God or whoever was listening that Sam didn't notice. So of course he did.

"Dean, what's wrong?"

"What? Oh it's nothing Sammy. Just thinking."

"Dean, you don't think."

"Rude."

"I'm just saying, you should probably tell me what's going on before I drag you down to Bobby's shop and make him force you to tell me."

Dean looked up at his brother who was wearing an expression equivalent to that of a flapper who's just caught her friend necking with a bootlegger.

"Sammy, I ..." Dean faltered as he wondered if coming home was even a good idea in the first place. At Sam's expression of utter concern (or maybe it was an 'I told you so' smirk) he unwillingly continued to talk.

"Sammy, I lost my job." Dean was able to spit out. "I don't have enough money to pay rent and feed the three of us."

The smirk on Sam's face faded and Dean watched him swallow as the gears in his mind turned.

"Sammy--" Dean started.

"Let's go," Sam interrupted, grabbing his coat off the chair.

"What?"

"I know a nice little speakeasy uptown. We're going for a drink."

"Sam, did you not hear anything I just said?"

"Don't get your panties twisted, I know the owner. She'll give us free booze." with a wink, Sam was out the door and Dean had no choice but to grab his coat and follow him.

_____~•~____

The speakeasy wasn't exactly the greatest joint in town. Located under a shoe shop uptown, people called the place 'The Roadhouse' even though you can't exactly get to it from the road. Inside, the dark bar smelled of smokes and booze and piss. Although Dean didn't mind, the place was filled with people like him, young, broke, and breaking the law just by being here.

The makeshift dance floor in the back of The Roadhouse held women and men alike, all dancing to some upbeat jazz song that made them look carefree. Right at the front near the door was the bar, wall stacked high with Canadian whiskey and the occasional beer. Busy place for such a low joint.

Sam dragged Dean directly up to the bar, squeezing past a group of drunk flappers who tried to pinch Dean's ass on the way by. He looked back and winked at them and heard several of them swoon.

"Dean. We're here to forget about our problems. Not cheat with some too-drunk hussy."

"I don't think she was a prostitute, Sammy, just well dressed."

That earned him an eye roll and a sigh before Sam ignored him to catch the bartender's attention.

"Hey, Ellen!" Sam waved at the older woman working behind the bar. She gave him a smile that made her eyes crinkle at the sides and turned to walk to them.

"Well, howdy, Sam! Long time no see, boys. What can I do for you?" Ellen smiled, absentmindedly wiping clean a few shot glasses.

"Remember that favor I did for you a while back?" Ellen smiled again and Dean whipped his head around to stare at his brother, if Sam was working for these type of people Dean was going to have none of it.

"Oh, yeah" Ellen replied, "Thank you for that by the way."

"Anyway I would like to cash in that repayment now, if you don't mind."

Ellen laughed, "Of course. A couple beers, on the house." She shouted to no one in particular.

As soon as she walked away Dean grabbed Sam's arm and hissed "What favor?"

Sam chuckled a little bit, "It's not like that, Dean. I did her taxes."

"Oh." Dean felt himself go red in the face. Of course his little brother wasn't working in the Rum Running business. He would have told Dean.

When Ellen came back with their beer, Dean politely smiled as Sam introduced him. When Dean registered the conversation had transitioned to boring Sam things, he picked up his beer and absentmindedly walked around the speakeasy, trying to pass time.

Ten minutes later his beer was gone and Sam was still talking. Dean made his way back through the crowd to the bar, being careful not to run into anyone (so, of course he did).

With a crash, Dean, a few glass shards, and another man were on the floor smarting and confused. Dean, being the first one on his feet turned to help the guy he ran into.

"My apologies!" Dean held his hand out to help the man still on the floor, "Let me help you up."

The other man grabbed his hand and Dean hauled him, wobbly, to his feet.

"Woah there." Dean said, steading him.

"Thank you," the man said looking up at him-- and holy shit, was he gorgeous. Dean found himself at a loss for words looking at the well-built man in front of him. His blue eyes were something bright in the dark bar and his dark hair stuck up in places that made him look like he just walked out of petting some dame in the bathroom. And his lips, although chapped like everyone's is in the Michigan winter months looked oh-so-very-kissable.

"Uh-" the man started, pulling his hand away from Dean's "Th- Thank you."

Dean watched him as he walked away, a bit more flustered than when he stood up. Breaking his gaze away, Dean started for the bar again, mind occupied with those oh so very blue eyes.

Sitting down at the bar, Dean explained to the second bartender, some guy named Ash, that he was with Sam and they were getting free drinks. And soon enough he was wolfing down his second beer of the night.

"Slow down there, son. People will think you're trying to start something."

Dean looked to his left to find an older man with thinning hair smiling slyly at him. He was dressed way too fancy for a juice joint like this and Dean immediately came to the conclusion that the man was a gangster.

Wanting nothing to do with the gangster, Dean merely nodded and looked back to his drink.

"Girl troubles or did you lose your job?" The man pressed.

“Yes.” Dean replied curtly.

Chuckling, the man held out a hand "Zachariah. You can call me Zach"

Dean smiled politely and cautiously shook his hand, "Dean."

"Well Dean," Zach said in a slightly more upbeat tone, "I can fix at least one those problems."

Dean looked back up at Zach who was smiling in that sleezy way again. He hoped to god he wasn't propositioning him.

"My...employer is looking for young men about your stature to deliver some... merchandise."

Dean set his glass down on the bar, "Your employer?"

"Yes. Michael Milton, maybe you've heard of him?"

Dean sighed, "You mean the Michael Milton who leads the Angellotte Gang downtown?"

"The same." Zach smiled again and Dean felt himself involuntary shiver, "What do you say, Dean? I promise you'll make twice as much as you did back at your last job." Zach held his hand out for Dean to shake again.

Swallowing thickly, Dean spared a glance back at Sam who was still animatedly talking with Ellen. Getting into gangs was suicide in the most literal sense, but he has to, Sam has to eat. Sam is his first priority.

Looking back at the hand stretched out to him, he took it and could practically feel his life being thrown upside-down.


	2. Not So Much Upside-Down as Flipped Normally

**Summary for the Chapter:**

> Shit happens and Dean's world falls apart.

**Notes for the Chapter:**

> Chapter 2 okay!! I tried so hard to get Cas into this chapter but no. Next chapter I swear to Chuck.  
> I'd also like to thank the same people as last chapter and here's one last friendly reminder that we loVE reviews so... Have at it!! <3  
> -Katie

The sharp clack of heels on the cement floor was almost welcome rather than the silence Dean had endured for the past hour. Today was his first day as a member of the Angellotte Gang and it, well... could be going better.

Most of Dean's afternoon had been spent sitting quietly in an empty warehouse downtown. Upon his arrival he was greeted by Zach and then told to stay put until they called for him.

That was over an hour ago.

Now, Dean looked up to see a pretty blonde walking swiftly towards him. Her dress waving in time with the clack of her heels on the cement. Dean stood up to meet her and he was met with a smile that reminded him of Ellen.

"Jo Harville." She held her hand out for Dean to shake, "You're Dean Winchester?"

"Sure am." Dean smiled.

"Good. Come with me." Jo turned on her heel and quickly walked back the way she came. Dean had to jog to keep up.

"You ever kill anyone before, Dean?" Jo asked when Dean caught up to her.

"Uh... No." Dean replied taken aback.

"Well, looks like today's your lucky day!" She turned her head to smile directly at Dean who swallowed hard.

"I thought this job was just moving booze across the border." Dean said darkly.

"Slight change of plans, babe." She winked as they reached the small door at the end of the warehouse. She looked at Dean one last time before quickly opening the door and sliding inside.

Dean took a deep breath before opening the door himself. Everything was moving too fast for him. For a moment he wished he was a child again. Sitting on his mother's lap before everything fell apart. Before his entire life moved too fast.

Dean shook his head, shaking out the childish wishes and opened the door with barely more than a click.

Immediately Dean was met with entirely new world. Artificial light flooded his eyes as sharply dressed men and women whisked past him yelling things that almost seemed like a different language. Dean noted the crates of illegal booze stacked high, ready to be loaded into cars and trucks alike. It almost seemed unreal that this is what he would do now.

Spotting Jo not too far away from the door, Dean weaved his way through the busy gangsters he now called his coworkers to join her.

"Golly," Dean muttered when he reached the place where Jo was standing.

"Isn't it something, Dean?" Jo smiled again, "Before we head out let me give you the grand tour." She grabbed his hand and dragged him through the people to a staircase on the far wall. She walked halfway up before stopping and pointing vaguely behind some cars.

"That's where you're supposed to be working," she said matter-of-factly. "I pulled some strings to get you with me. You're too good to work there anyway."

Dean chuckled and watched her point up the stairs, "There," she said again, "is where the best of the best work. They handle the trades, the allies... and the kills. That's where the big man works. Michael Milton. Running co-pilot with his sister Anna." Turning back to Dean she added, "Nice girl. You'll like her."

"With a brother like Michael I don't think I should like her how I'm planning."

Jo laughed loudly before jumping back to reality with a short "Oh!" She grabbed Dean's hand again and dragged him down the stairs and under them to a group of people sitting and laughing as if they weren't doing anything illegal by breathing this air.

"Dean," Jo smiled again, "These are your new best friends."

"Uh?" Dean questioned waiting for an explanation.

"These are least jerk-like people in the entire business. And with a sense of humor like yours, you'll love 'em." Jo took up pointing to them as if Dean could remember who was who, "This is Gabriel, Balthazar, Krissy, Hael and Charlie."

To Dean, the names and the pointing ran together too much and he could only remember that Krissy was the youngest one, (maybe fifteen, golly) Charlie was the redhead with the short skirt and Gabriel was the one holding a bag of sweets like a baby.

"Eh." Dean replied hiding the fact he missed most of the introductions, "I'll get it eventually."

That earned Dean a few chuckles from the group. They were odd, he noted. A mixture of strong men, skinny men, pretty dames and girls who looked about fifteen. Dean figured in a few days he'd fit in just fine.

"Jo!" The one named Charlie piped up, "Get going! You're an awful shot when it's dark."

"Right okay. Let's blouse, Dean!" Jo grabbed his hand once again and dragged him away from the group and towards a car.

"Shoot straight, babe!" Dean heard someone from the group shout after them.

And just like that Dean felt his heart drop.

He was going to help this girl kill someone.

_____~•~____ 

"Nervous, Dean?" Jo asked him once they were driving quietly through snowy Detroit.

"Nah. It's just hunting. But with bigger animals," Dean joked, trying desperately to hide the fact that he was actually scared to death.

"Hm. Didn't think of it like that." Jo said, turning onto another obsolete street.

"We'll then how do you think of it?"

"I dunno... the job no one else wants to do? A reward for being a great Rum Runner? My job?" She chuckled to herself, "Truth be told I'm a better Rum Runner than anything. I don't even want to do this. Nobody does. But say no to the big cheese and you'll be next on the list."

"Why did you drag me into it?"

"Oh Dean, honey. If I'm going down, I'm going down swinging with a pretty boy linked at my hip," she winked, and turned once more before she stopped in an alley outside a general store.

Shutting off the car, Jo sighed loudly, "Ready, Pretty Boy?"

"As I'll ever be." Dean smiled in reply.

Jo reached into her coat pocket and pulled out a photo, a knife and a small gun. She handed Dean the photo before she turned and loaded the gun.

"That's our guy." She said vaguely pointing to the picture in Dean's hands, "Owns the store. Real sleazy jerkwad. Stiffed Mister Milton over on a deal. And it's our job to shoot him in the face. His store closes at 6, we got 5 minutes before he walks out that door, and you stab him in the back."

"What are you gonna do?" Dean asked.

Cocking the gun dramatically, Jo smiled, "I'm gonna blow his brains out."

Minutes later, a rather tall, clean shaven man, dressed in a nice three-piece suit and an expensive fedora walked out of the General Store whistling some nameless tune.

Dean and Jo quietly made their way out of the car, weapons hidden well enough so the looked like any other average joe.

When the man turned the corner into the alley, he spotted Dean and Jo and innocently tipped his hat, "Evening." He greeted.

"How do you do?" Jo replied without a smile.

Thinking nothing of it, the man kept walking. As soon as his back was to the pair, Dean leapt into action.

He drove the knife into his target's back, feeling it penetrate skin. Dean felt warm blood spill over his hand, a contrast to the cold air around them.

However, he was unprepared for the retaliation. The man whipped around and socked Dean in the face something good. Barely fazed by the blow, Dean immediately whipped around and punched him back, knocking the man onto the ground, and onto the knife still embedded in his back.

The man's howl of pain was cut short by a gunshot coming somewhere from behind Dean.

And just like that it was over.

Dean turned around to see Jo holding the smoking gun in her surprisingly steady hand. She smiled that eye-crinkly smile again.

"Has anyone ever told you that you are really attractive when you fight?"

"C'mon, lets go." Dean said quickly.

The pair jumped into the car, and soon were back on the road in silence, Dean in the driver's seat, visibly shaken.

"What was his name?" Dean asked breaking the still silence.

"What?" Jo said, surprised.

"The man we just killed, what was his name?"

"Dean, it's better you don't know. He was just a nameless man. He's nameless, we're nameless. It's simpler that way, if you're nameless no one cares if you die."

"Jo."

She sighed and picked up the paper that had been dropped hastily onto to the floor, "Dick Roman," she read, "no known family. There, you happy?"

"No." Dean replied, unconsciously tapping his fingers on the steering wheel.

Jo sighed, "It gets easier you know... breaking the law. Murdering. Blatantly lying to people who trust you. Canadians." She chuckled at her own joke.

When Dean didn't reply she continued, "Eventually it's just something you do to get paid. Just another paycheck."

_____~•~____ 

Four paychecks, three weeks, and eight runs to Canada later, it had become easier for Dean. He was feeding his makeshift family and that was all that mattered.

He even had a little extra money left. So he bought Sam a bow tie, ("Dean, I don't even have a suit.") Bobby a bouquet of flowers, ("You're an idjit, boy.") and Lisa an engagement ring.

And one of these things was the worst idea he's ever had. (And it wasn't the flowers, despite all of Bobby's griping)

Dean blames bad advice.

"Oh, I think that's a great idea, Dean-o!" Gabriel said brightly, slapping Dean's back with a little more force than necessary.

"Yeah, Don't listen to him Dean," Balthazar piped up from on top of a stack of crates, "He thought necking with the border patrol agent who caught us smuggling booze was a good idea."

"He let us go, didn't he?"

"After he gave you a black eye, and Krissy paid our way out."

"Happy to help!" came the teenager's reply from somewhere on the stairs.

"I'm on the verge of high-tailing it to Vancouver and becoming a fisherman if no one gives me any real opinions." Dean sighed.

"Do it!" Charlie shouted behind him before jumping on his back and continuing from her new perch, "If you do it I'll bake you a cake. And if you do it and she says yes, I'll sneak so much whiskey out of Canada for you, I'll be finding it in my panties for weeks!"

Dean set her down and then turned to face her, "You swear?"

Swiping a piece of her short red hair out of her face, she replied, "I swear on the Governor's booze-soaked bedspread!"

"Attagirl!"

Dean grabbed his coat and headed for the door. Hael's confused, "Did they do the bedspread thing again? I'll never understand the bedspread." kept him laughing the whole walk home.

_____~•~____ 

"Lisa? You home?" Dean half-whispered, half-shouted as he opened the door. All day, he hadn't been able to wipe the nervous smile off his face. Everyone at work knew what was happening tonight.

"Yeah, Dean! In here!" came his girlfriend's reply from the kitchen. It was a modest area, with barely enough room for more than one person to cook. The sink was running, Lisa must have been cleaning up from dinner.

Dean shut the door with barely more than a click. He took off his coat and set it on the nearest chair, spotting Lisa in front of the sink. Just as he's guessed, she was washing the dishes that she and Sam used for dinner.

Dean, being the ever-so-wonderful-boyfriend that he was, walked up behind his girlfriend and hugged her tightly from behind. He had never been one to get nervous, but he could feel his heart pounding in his head. He reminded himself that there was nothing to be afraid of. It was only Lisa.

"Good evening my dear," Dean hummed, "I'm assuming Sammy is tucked in and sleeping like a rock?"

Lisa laughed, "Dean, Sam's eighteen and it's 7:30. He's out."

"Ah, even better." He smiled as he moved to pepper kisses along the side of Lisa's neck, his breath unsteady. Dean wanted to kick himself. He had aided in a murders without so much as a second thought, and now his palms were beginning to sweat as he kissed his girlfriend. Dean was starting to think he was losing his mind.

"Someone's very clingy tonight," Lisa laughed again, turning around in Dean's arms. Usually, she'd have to trick her boyfriend into being this loving. "Bad day?"

"Actually, quite the opposite," Dean still couldn't hide his smile as he let go of Lisa's waist. "I have a quick question to ask you."

"Do you now?" Lisa beamed, her tone still unsuspecting but her eyes glistening with excitement. Dean wasn't one for surprises.

"Lisa Braden, how would you like to be Mrs. Lisa Winchester?" He pulled the ring he bought out of his pocket and held it up for Lisa to see.

"Dean!" Lisa gasped. Her initial excitement was quickly wiped from her face when she saw the stone shimmer in the dim light. "Where did you even get this?" She asked, motioning to the ring. Lisa's feelings seemed hidden in surprise as she bent inward to get a closer look, noticing the size of the diamond that had been offered to her.

"I bought it, dummy." Dean smiled wider as Lisa's jaw dropped. This, she knew, was not something they could afford.

"How?"

"With money."

The surprise faded from Lisa's face, bending itself into a look of disapproval. "Dean. Three weeks ago we barely had enough money to pay rent. Where did you get this money?"

Dean dropped his hand. They had gone over this all too many times recently. He couldn't tell her about his job, but it was hard to go home lying. The blood on his hands couldn't be washed away forever. He knew that. But for now, it was better to keep his position to himself. For Lisa's sake. "Lisa," he began, trying to form a coherent response. "Babe, it doesn't matter-"

"Of course it matters, Dean!" Lisa started to yell. This, Dean could tell, had been the last straw. Lisa was done with playing his games. "If you want me to be your wife you have to stop being so secretive! You never tell me anything, ever. Especially these last few weeks. Hell, I don't even know your father's name!"

"It's John." Dean spat, the name feeling dirty on his lips. He snapped the ring box shut, curling his fingers tightly around it. Lisa scoffed.

"Well, it only took you a year and a half to tell me!"

"So are you saying you don't want to be my wife?" Dean asked, knowing immediately how desperate the question sounded. He felt vulnerable and exposed. Dean had opened himself up to Lisa, and now she was taking advantage of it. He realized he was starting to yell too, but he couldn't bring himself to care. Dean wasn't pleasant to be around when he'd allowed his feelings to be hurt. "A simple 'no' probably would have been a little nicer."

Lisa just rolled her eyes. She wasn't about to back down now. "I want you to tell me where you got this money!"

"Can't you just be happy that I'm actually making money for once?"

"Dean Winchester!" Lisa snatched the box out of his hand, holding it out like a dirty rag. "Tell me where you got the money for this ring right now!"

"Fine! I joined a gang. I lost my job, I joined a gang. I'm a rum runner!" Dean threw his hands up in defeat. "Happy?"

At this, Lisa actually laughed. At first it was quiet, nervous, like Dean was about to admit this was all a joke. But when he stayed stationary, she began giggling uncontrollably. Her face grew pink and she bent over, hiccuping. "You honestly expect me to believe that?" She asked between short breaths, trying to regain composure.

"I'm not lying to you," Dean responded, his expression somber. Lisa straightened up and sniffled, her fit subduing and mouth curling into a frown. The realization was written on her face, and became clearer when Dean did not burst out into laughs of his own.

"So you were asking me to be a moll without me knowing?" She hissed.

"Not if you said no."

"Well I am. This is me saying no." Lisa threw the ring on the floor, listening to it hit the tile with a thud. "Jesus, you're insane. Dean, you're insane!" She began to reach for her bag.

"Well then what are you gonna do?" Dean said quietly, all the anger in his veins gone.

"What does it look like I'm doing? I'm leaving. Keep my things. I don't want 'em." She grabbed her coat off the rack and threw open the door. "I hope the next dame you con into loving you is a lot stupider than I am." She slammed the door as hard as she could, making the portraits on the wall shake. But she didn't leave before shouting through the walls, "I HOPE YOU ENJOY DYING LIKE A GANGSTER, DEAN WINCHESTER."

Dean threw a plate at the wall where he heard Lisa's voice in a half-hearted rage. He didn't care, they wouldn't need the third one anymore. Cleaning up the broken ceramic would give him a distraction. But as the porcelain crumpled onto the floor in front of him, he sank to the ground in sudden realization. Everything was falling apart, just when he was beginning to think things were becoming normal.


	3. The One Where Repressed Gay Feelings Are an Issue

**Summary for the Chapter:**

> Dean is a burrito of sadness until Castiel Novak (FINALLY) comes along. More shit goes down.

**Notes for the Chapter:**

> Oh hey, it's Maddy! This is the first chapter I wrote the majority of. I hope you like it! Thanks to Riley who is a lovely beta and Katie, who wrote the previous chapters and is an A+ person. Be cool and review this because I'm needy and need reassurance?? (:  
> -Maddy
> 
> Hello also since we probably won't get another chapter up before Christmas... HAPPY HOLIDAYS. Even if you're reading this in the middle of summer throw yourself a Christmas party because you deserve it. <3  
> -Katie

It had been almost two months since Lisa had walked out. The days were going by slower than ever, dragging on as Dean tried to keep his secrets from Sam. 

Charlie had upheld her promise and baked Dean a stupid cake, the words “sorry” written in messy blue icing across the top. His new friends were the only thing that seemed to be giving him solace. Sometimes they stayed at the speakeasy after a long day at work, just drinking and talking. They began trading their secrets with each other, confessing regrets and indulgences over the good liquor.

After the breakup, Dean became more ruthless in his assignments. He was sent out almost every day, no longer needing a partner. They trusted him to do the job right. Before long, he was off of the unwritten probation he had started on and became an equal. He passed along hundreds of bottles of alcohol on routine, the clink of the glasses tapping against each other becoming as common as his footsteps. He left no fingerprints, and only allowed himself to feel remorse for the crimes he committed when he was alone, tucked between the sheets of his bed, Sam asleep and unknowing in the next room.

In this business, people moved in and out quickly. Apart from his core group, Dean saw unfamiliar faces wherever he looked. The best thing about this business was the blindness of the bosses. Never in his life had Dean seen such diversity in a workplace. Beautiful girls with short skirts, coffee-colored eyes, and olive skin partnered with stocky, pale men who refused to wear any sort of suit. But honestly, after a while, they all became a blur. It was pointless for Dean to get himself involved in any sort of casual affairs. They would all end badly. Gone were the days of spending nights at stranger’s houses. He hadn’t woken up hungover and covered in hickeys since he was fired from the garage. Dean winked at striking faces, but never reached out to touch. He was learning the art of reclusiveness.

The start of April proved to be a slow time for Dean’s assignments. He was becoming bored of being pent up in the speakeasy. He tried to tell himself that it was better than smuggling things into the country, but honestly, he was beginning to long for the predictable visits. He missed the race in his heart when he returned back to the warehouse with successful news. Instead, he was tapping his fingers on tabletops, watching Krissy and Hael try to dance behind the counter (Ellen never allowed them out on the dance floor) when he heard the click of Jo’s telltale footsteps coming down the hall.

“We have a guest,” she announced, appearing at the doorway with a man by her side. He was tall and unsmiling, standing awkwardly next to Jo like he wasn’t sure what he was supposed to be doing. Dean looked up from his spot on the stool. He recognized those bright eyes immediately, although he could not remember for the life of him where from. Good-looking people passed by every day in this place, but not like this one. The man’s gaze caught his, and Dean swore he saw a look of matching recognition.

“This is Castiel Novak,” Jo introduced, "Don't scare him just yet," she paused for everyone to mutter their halfhearted greetings before turning to Dean and continuing, “Dean, this one’s yours.”

“Wait, what? Huh?” Dean stammered, finally breaking his stare with the new man.

“I said he’s yours. As in he’s your new partner. Zachariah sent him in with me. I’ve got an assignment for you two.” Jo looked from Dean to Castiel and back again, waiting for either one of them to say something. Sighing impatiently, she bumped Castiel on the arm to give him a little push. “Go on, Blue Eyes. If you guys don’t hit the road soon the boss will be pissed.”

Castiel nodded, following Jo to the counter and taking the stool next to Dean. Jo handed them a slip of paper, which Dean immediately stuffed in his back pocket. 

"There isn't much today boys, demand is low," Jo explained, "Either people are just too darn broke nowadays or all our clients are getting too smart and too sober." Laughing at her own joke she continued, "You guys can take the ferry to--"

“I know where we’re going, doll.” Dean interrupted with a smile.

"Alright, pretty boy!" Jo perked up and Dean turned his conversation to Castiel, “Lets get a wiggle on, it's a big night for you.”

____~•~____

The journey to the lake from the speakeasy was short, and Dean knew the way with his eyes closed. On these assignments, he was allowed to drive Zachariah’s expensive cars. Even though his job at the garage had ended long ago, Dean still had a fascination with vehicles. He loved the click of the motor filling the silence.

Castiel didn’t seem to know much about the job going in. So far, he’d been quiet, following Dean without question. He didn’t speak up until they were in the car, almost halfway to their first stop.

“Where are we going?” He asked, his voice muffled over the motor.

“We’re headed to the border. That’s where we pick up the booze.”

“How do we get there?”

“We have to take a boat. It’s not far though. Maybe twenty minutes.”

“I did not think it would be this nerve-wracking,” Castiel confessed, even quieter now. Dean took his eyes off the road to catch a glance at him. He really was beautiful. His hair stuck out at different angles, messy from the fedora he was wearing earlier. Dean was struck with an aching desire to reach over and run his fingers through it. He tried to shake the thoughts away—it was sleeping with another man that got him kicked out of his last job, and Castiel was a coworker. Dean was just starting to find his place in the gang, and he didn’t want to take any chances.

“You’ll be fine, Cas,” Dean replied, hardly giving thought to the nickname he had given him. It just came naturally. “It’s not as dramatic as you think it will be.” 

Cas nodded, trusting Dean on his word as they pulled up to the dock. They left the car and Dean walked straight passed the men collecting tickets. It was obvious that they all knew each other- Dean had done this round countless times before. Cas followed close behind, no one questioning him as he freely boarded the boat.

“Do we need tickets?” He questioned under his breath.

“Nah, those boys are regulars at the speakeasy. They started letting me by for free after a month as long as I gave them free booze when they came in.” Dean spoke in a hushed tone, but he wasn’t too worried about people listening in. Most of the people on this ferry traveled often, and no one ever asked about destinations.

They were still standing when the boat when it lurched and began running. Cas reached out and grabbed Dean’s arm to steady himself. “m’sorry,” he muttered, regaining his balance. His cheeks were flushed pink. “That caught me off guard.”

“Don’t worry about it. You probably just haven’t gotten your sea legs yet.” As Dean responded, he realized Cas’ hand was still holding onto him. Instinctively, he leaned into the touch. For what seemed like much longer than a minute, the two were left staring, studying each other’s faces. Cas’ eyes rested along the curve of Dean’s lips and he could feel himself beginning to blush. He pulled away, forcing himself to remember that they weren’t the only two passengers on the boat. “We should find a seat.”

Dean led him to the back, to two empty seats where he usually sat alone. Here, Dean could feel the splash of water from the motor hitting his face. It made him feel alive. Cas stumbled a little before finally sitting down, his shoulder close enough to Dean’s that they were brushing. “It gets easier to walk around after a while,” Dean reassured him. Cas just laughed a little, looking down at his feet.

“Dean, I lived in New York. I can’t tell you how many times I’ve taken the Ferry out to Ellis Island in ridiculous thunderstorms,” he looked up now, grinning at the memory. “Your little lake is nothing. It’s just been a while.”

Dean laughed, wiping the water droplets from his forehead. He made a mental note to listen for any trace of New York in Cas’ voice. Somehow, the possibility of it was exciting. He imagined himself kissing the accent right out of Cas as he whispered against his mouth, asking him if he had any “cawhfee” for the morning. “Why were you in New York?” Dean asked quickly, hoping to distract himself.

“I grew up there, but I stayed to act,” Cas confessed, his eyes returning to a bolt on the floor of the boat. “I didn’t get very many jobs though. So I ended up here instead. Where are you from?”

“Here.”

“Here in Detroit?”

Dean hesitated. “Well, we moved around a lot when I was younger. But after a while, we just kind of settled here. Made it our home. And I like it.”

“Who’s we?”

“My little brother Sam and me,” Dean replied, shrugging his shoulders. He had worked hard to forget his past; to give Sam a better life than he had gotten. It had been difficult, and Dean certainly hadn’t expected to join a gang, but this was the happiest he’d been in a while.

“What about your mom and dad?” 

Dean wasn’t good at being interrogated, and he was even worse at talking about his family. “You ask a lot of questions, Cas,” he smirked, avoiding the question. “What about your mom and dad?”

Cas shrugged, his face falling. “We don’t really talk.”

“Oh. I’m sorry.” Dean was quick to forget that he wasn’t the only person who had a bad relationship with his parents. He felt bad for asking, but brightened when Cas responded with a smile.

“Don’t be.” Cas stood up and turned around, looking to the front of the boat. “I think we’re almost there.”

Dean nodded, following Cas’ lead and getting on his feet. He felt a little shakier this time; he hadn’t been on the boat in weeks. “Alright. Here’s what’s going to happen. When we get off, the guys are going to be about a block away. We’re each gonna have two boxes to carry, and you’ve gotta be careful with them. This boat will leave again in another half hour, so we have to make this as fast as possible. But if we’re waiting back here for too long, they’ll ask us what we have in our cases. Some of the officers around here are starting to recognize me.”

Cas listened intently, gripping the side of the ferry as he did. Although he wasn’t sure he would admit it, Dean was pretty sure this was the most dangerous thing Cas had done. The two began moving towards where they would get off. Dean still led the way, Cas following close behind. The boat lurched, sending Dean stumbling backward—over his shoelaces and onto the floor.

“Are you alright?” Cas asked urgently, holding out his hand to help Dean up.

Dean tried his best to hide his blush. “Fine,” he responded, taking Cas’ hand. Once he regained composure, the two began walking to the front again. 

“I promise I won’t do that when we have boxes of glass bottles,” Dean joked.

“Don’t worry, Dean,” Cas responded, laughing and bumping him on the shoulder. “I’ll be there to catch you again when you do.”

“Catch me? My ass hit the ground. I don’t think that qualifies as catching,” Dean challenged.

“I practically raised you from perdition,” Cas replied with a scoff. “Don’t minimize it.”

Dean grinned, reaching the exit and holding onto the railing there, making sure he didn’t fall again. The boat reached a stop at the dock and was anchored in place, Dean and Cas were the first ones out. Dean’s pace quickened and he took sharp turns, knowing exactly where his mission led him. Cas followed close behind. When they reached the distillery, a shadowed figure appeared.

“Hey Dean,” it spoke, emerging from a dark space and allowing the orange evening light to hit his hair. He was thin and smiling. “I haven’t seen you in so long. I was staring to thing that Michael didn’t want to work with me anymore… do you think he still likes me? I mean, us. As a distillery. I’m worried. Anyway, eh, who’s your friend?” 

“Chuck, relax. I don’t think Michael has anything against you guys. People are just buying a little less right now. Things will be back to normal in no time,” Dean explained calmly, shaking the man’s hand. He had missed meeting up with Chuck, even if they only spoke in these small bits of exchange time. Chuck was constantly nervous about these assignments and Michael’s responses, which made Dean feel better about his own worries. Back here, he felt like he was the collected one. He was in charge. “And Chuck, this is Cas. He just started, so I’m showing him the ropes.”

Cas held out his own hand for Chuck to shake. “You can call me Castiel,” he told him, as if he wanted to save his nickname just for Dean. It made Dean’s stomach flip, and he tried his best not to blush again.

“Thanks for this, Chuck,” Dean spoke, turning on his heels. They had to make it back to the boat on time, and it was getting late. The sun had long since settled on the horizon and was beginning to dip below the lake. Sunsets in Canada were more beautiful. They reflected perfectly on the water, and Dean treasured the days where he would catch a glimpse of them.

"Dean?" Chuck questioned, pulling Dean out of his thoughts.

"Yeah?" Dean responded maybe a few seconds too late.

Obviously confused at the lack of conversation Chuck shrugged and said, “I know you two have to get back to the boat soon, you want the boxes?”

"Oh yeah yeah." Dean smiled, "C’mon Cas." He motioned vaguely for Cas to follow him.

The pair followed Chuck through his distillery, the artificial lighting growing brighter as the sun set out the window. The distillery wasn’t very big, but it got the job done. Dozens upon dozens of crates of booze were sent out daily to other parts of the county from this one place, Dean almost felt disappointed that they were taking such a small amount back to Detroit. They didn’t even get to take out the speedboats Dean loved to drive so much. Still, Dean felt bad. It was kind of an uneventful run for Cas’ first time out compared to his.

Speaking of Cas, the man was continuously quiet beside him. Obviously nervous, Dean really didn’t know how to comfort him. Maybe a “Hey it’s alright. We won’t get shot in Canada.” or a touch of his hand to his shoulder as a purely comforting gesture.

And ONLY a comforting gesture, of course.

"Ah here you go, Dean!" Chuck smiled, reaching a truck packed high with crates of whiskey, "I’ll have one of my boys drive it down to your boat for you."

Out of the corner of his eye, Dean saw Cas pale. He chucked, “Actually Chuck we only need four boxes. There isn’t very much demand at the moment.”

"Oh." Chuck’s face fell, "I still get paid right? Michael isn’t letting me go is he? I don’t think I could deal with more gangs trying for my attention, it was murder last time. And I mean literal murder—"

"Chuck." Dean tried to mask his laughter, "Your money is in the post now. Can we have our boxes? We gotta get back."

"Yeah. Just take em." Chuck smiled. "I see Becky trying to wave me down. I’ll see you guys around!"

"Bye Chuck!" Dean waved.

"Goodbye," Cas muttered almost too late.

"C’mon Cas!" Dean said, handing Cas a box, "Lets get those muscles moving! It’s a long walk back to the ferry, can you make it?"

Cas scoffed much like Dean has heard Krissy do on occasion, “Of course I can, Dean,” another box was stacked on top of the one already in his hands, “I picked _you_ up, didn’t I?”

Laughing, Dean looked up at Cas’ adorable smug face. “You’re not gonna let that one go are you?”

"Never."

Dean picked up the last box, and walked out of the distillery back towards the docks. Imagining himself kissing the smirk right off of Castiel’s big smug face. Dean silently reminded himself to tell Cas to smile more often, it looked good on him.

_____~•~____

It was dark by the time Dean and Cas returned to Detroit, an eerie chill settling in the dark streets of the bright city.

Rather than have a teenaged worker at the docks bring their car to them, despite Cas’ protests, the two men walked silently side-by-side to the car. (Which happened to be very inconveniently parked a few blocks away.)

In the darkness there was an unmistakeable stillness in the air that even Dean felt cautious about. A quiet that reminded him of the calmness before a giant thunderstorm. Tensions where high, so there wasn’t as much as a thought to protest when Cas suddenly was walking closer to Dean. Close enough so that Dean could feel the heat from the other man, radiating from under his tan trenchcoat.

Something was going to go very wrong. Dean could feel it.

As the two turned a sharp corner onto a darker street those tensions snapped. Dean heard the men in the shadows before he saw them, and he wished he could have done something about it.

A cold knife was suddenly pressed to the back of Dean’s neck by a man he couldn’t see. He assumed the same had happened to Cas, judging by the terrified gasp he heard him produce.

"What’s in the crates?" The man holding the knife to Dean hissed.

"None of your beeswax" Dean spat back.

Pressing the knife a bit harder into Dean’s neck, the man laughed coldly, “We know who you are, Dean. So tell us what’s in the boxes or we’ll bump off both of you right here and now.”

"Try me" Dean dared.

"Leave it alone, Mac. We gotta get back now. Just take ‘em."

The knife moved quickly and disappeared from Dean’s neck to being imbedded in his shoulder. Hissing with pain, Dean’s hold on the boxes in his hands slipped and the boxes fell to the ground with an unmistakable shatter. Behind the loud shatter of the bottles, Dean barely registered a terrified “Dean!” from his new partner before that too was cut off by a hiss of pain, much like Dean’s own.

Except Cas was still able to hold onto the boxes.

Regaining his composure, Dean turned around and punched the man who’s knife was currently embedded somewhere in Cas’ flesh. The man fell over backwards and made a move that made it seem as if he was ready to strike the pair again. But in a movement almost too fast for Dean to catch, Castiel threw the boxes of booze still in his hands onto the flailing gangster. As the bottles shattered on top of the man, Cas was suddenly holding Dean’s hand and they were running the opposite way.

“Dean,” Cas spoke again, more broken this time.

“It’s okay,” Dean replied. “You’re okay. Just keep running. We’re almost to the car.”

And he was right. He could see the shimmer of the shiny hood in the moonlight and he thanked God they hadn’t parked any farther away. Cas was beginning to stumble, and Dean didn’t miss a beat. He threw the man’s arm over his shoulder and carried his weight the last few feet, setting Cas in the passenger seat as carefully as possible.

“Where are you hurt?” He questioned, trying his best to remember the first aid he once knew.

“Don’t worry, I’m okay,” Cas replied, adjusting himself in the seat. “I’m going to get blood on your car.”

Dean shook his head, using his sleeve to wipe off a line of blood trailing down Cas’ forehead. “It’s Zachariah’s car, it’s had blood in it before,” he assured him. Cas just nodded, leaning his head back on the seat. He didn’t look too beaten up. The blood on his forehead was just smeared, no wound was near there. He had been stabbed in the shoulder. Painful, but not fatal. Dean had a cut of his own in his arm, but he was used to minor injuries like these by now.

“I need you to take your shirt off,” he said, blushing even in the circumstances.

“What?” Cas asked, squeezing his eyes shut. “I thought you’d take me out to dinner first.”

Dean rolled his eyes, but his stomach flipped all the same. “I’ve gotta see the cut to know how to fix it, Cas.”

He shrugged off his coat and began unbuttoning his shirt obediently, wincing has his arms moved. The blood stains had made the wound look worse than it was. Dean took Cas’ shirt and pressed it over the area, trying to be as cautious as possible.

“Can you hold it there while I drive you home?” He asked. Cas held the fabric in place in response and Dean hurried over to the driver’s seat, jamming the key into the ignition. Cas gave him directions as he drove, and Dean silently hoped that this experience wouldn’t drive him to leave the gang. He wanted to keep seeing him, to watch him scurry around the warehouse and dance, drunk and careless, in the speakeasy. He didn’t want to see him like this, bloody and grimacing by his side. He promised himself to keep Cas out of danger, on the notion that he would return. The daydreaming had gotten away from him, and before Dean knew it they had reach Cas’ driveway.

“When you get inside, you need to wash that out. Do you have any alcohol? Use that, it’ll hurt but it will disinfect it. Keep pressure on it for a while. If you need any help, you can call me.” Dean explained, scrawling his telephone number down on a piece of paper. “Don’t go to the doctor without talking to me first. They’ll ask questions.”

Cas nodded, trying to shift his weight with his good arm while still holding onto the shirt. Dean offered to help him inside, but Cas assured him that he would be fine.

“Thank you,” he added, giving Dean a crooked sort of smile. “Really.”

“I almost got you killed,” Dean replied, “but I guess you’re welcome.”

And before Dean knew what was happening, Cas had leaned across the seat and pressed a kiss on his mouth. This way of thanking him was more effective, to say the least. It was chaste and their lips were chapped, but Dean felt the fireworks all the same, starting in his stomach and spinning around in his head. He had forgotten how amazing it felt to kiss someone so beautiful, and as Cas pulled back, he wanted to pull him closer. Hold him there for years.

"Sorry," Cas muttered before completely leaving and shutting the car door behind him. 

“Hey, I’ll see you soon!” was the only thing Dean could manage to say as Cas started towards his front door, obviously hearing him if the spring in his step, despite his shoulder, was anything to go by. 

He tasted like Castiel the whole way home.


	4. Do you even care if I title these correctly. (The one where they do the do)

**Summary for the Chapter:**

> Shit happens and Dean finally gets some

**Notes for the Chapter:**

> WOOOO YEAHHHH SMUT IN THE CHAPTER LETS GO. Maddy wrote most of it, so review let her know what you think, unbeta'd for this chapter, sorry dears. Enjoy!!  
> -Katie

Everything up to this point, Dean had considered an accident. Joining a gang, proposing to Lisa, heck, maybe even buying Sam a bow tie was an accident. As far as Dean was concerned, his whole life might as well be an accident.

But as he sat watching Cas laugh heartily at some story Gabriel was telling, he thought maybe that falling for Castiel wasn’t the worst accident he had. Maybe it really wasn’t an accident at all.

"And then-" Gabriel fell into another laughing fit again, "I told him that it wasn’t even booze."

The group of gangsters howled with laughter, Dean just smiled, missing most of the story while he was lost in his own head, he had no idea what they were even talking about. He did know, however, that Cas’ laugh was borderline beautiful, and the little crinkles that appear around his eyes when he laughed had captured Dean’s attention.

"Winchester!" Gabriel snapped his fingers in front of Dean, effectively breaking his probably too-long state at Cas.

"What?" Dean rolled his eyes.

"Quit making goo-goo eyes at my brother and listen for once, will ‘ya?" Gabriel laughed

"I was not making— Wait he’s your brother?"

The group fell into another laughing fit, making Dean’s cheeks flush red. Dean wanted to crawl into a hole and die until Gabriel made it worse. He was clutching his stomach and wheezing, and finally he managed to say, “Do you ever listen? My last name is Novak, you think I married Cassie or what?”

"No I—" Dean tried to retort but Gabriel wasn’t finished, "Does this mean you don’t really have a brother? Winchester number two is actually your son isn’t he?"

"He’s my brother, asshat. And besides, how did you know I even have a brother? I’ve never said anything about him."

"I know everyone," Gabriel smiled, putting his hands behind his head and leaning back on some crates, "It’s not like Winchester is the most common name in Detroit. Besides someone that tall and that pretty is rather hard to miss."

"How pretty are we talking?" Hael piped up from next to Krissy.

"No." Dean practically snapped. 

"He's about the same age as Hael isn't he?" Charlie laughed, "Oh my Lanta they would make the cutest couple!"

"He's got a girl!" Dean practically cried.

"Death can be arranged." Hael said quietly, making Gabriel double over with laughter.

"No matter how much you want to arrange a death, my dear angel, you still have to go through me." Said a soft voice Dean didn’t recognise from behind him.

"I can sure try to go around you, Ms. Milton" Hael smiled brightly as Dean turned around to look at the source of the voice. Immediately his stomach dropped, Anna Milton, the gorgeous, red head, sister of Michael Milton stood directly behind him. She had a powerful look about her that couldn’t even be stopped by the short flapper dress hugging her waistline. Dean wouldn’t admit it, but he was a little intimidated by her presence.

But then she said something that only made his gut drop further; “I need to speak to Dean Winchester and Castiel Novak.”

The chatter through their little group of gangsters came to a halt as everyone turned to stare at the pair. Dean spared a look to his partner who had reacquired the same look of terror he saw on the boat a few nights ago. Standing up slowly, Dean gave a swift nod to Cas who quickly followed his lead, and soon the pair were following Anna Milton up the stairs of the warehouse and into a plain room.

Now, Dean could clearly read Cas’ expression. And it said something like ‘she’s going to kill us in here and no one will ever find the bodies’.  
Which was probably true. Dean mentally went through a list of everything he had done wrong the past few days; losing booze to some sleezeballs his first run out with a new partner, failing to report injuries, sneaking a few bottles of booze out for himself, kissing his male coworker, and oh yeah, _wanting to kiss him again_.

"You can lose the look of terror, Novak, you aren’t in too much trouble." Anna said, shutting the door to their only escape route.

"Too much?" Castiel squeaked.

"Well, you think you can get away with losing your entire haul of booze on your first night?" Anna asked, and Dean heard Cas’ jaw snap shut, "But, I like you. And I like Dean. And I’m not blind. I can see the both of you were injured in the attack, and Dean over here is new with working with a partner." Anna turned her attention to Dean now, "I’m assuming you put Novak’s well-being in front of the job, am I correct?"

Dean nodded swiftly and Anna smiled, “As a person I can respect that. However as your employer I am required to tell you that was stupid and you should be fired.”

Dean swallowed thickly and nodded in understanding. He was alright with the idea of losing his own job, but Cas’? Dean was about to say something to defend Cas’ job, but Anna spoke up again, “However, I’m not going to fire you. The gangsters who attacked you? They were from the Hellfire Gang. Mac Lowery and James Campell. Better known as Crowley and Azael O’Malley. I don’t know what you boys did, but both brothers were major players in the Hellfire Gang. I just got word that Azael died last night from several broken ribs and a hole in his lung, and Crowley is devastated, won’t leave his home. Which leaves a major hole in their operations. And as a thank you for your service… I’m not firing you.”

Dean let out a breath he didn’t know he was holding, “Thank you. Thank you.” He smiled shakily.

Anna smiled and rolled her eyes, “Now get out. I hear Jo has a new assignment for you two. And be aware I won’t be as generous next time you lose our booze.”

"Thank you." Cas smiled once more before following Dean out the door. When Dean finally stepped out into the hall and heard the door click behind Cas, he turned around and threw his arms around his partner and hugged him tight.

"I’m sorry Cas. I’m so sorry." Dean breathed into his shoulder.

"It’s alright, Dean. We didn’t get fired." Cas chuckled squeezing his arms tighter around Dean

"Yeah but we almost did."

"Oh, shut it. It was an accident. Besides, I bet my arm would be gone if it weren’t for you. Thank you." And right there, Dean could have kissed him again. His blue eyes were even bluer in the dim light of the hallway, and Dean’s eyes flicked down to his perfect, kissable lips. They hadn’t said anything about the kiss they shared a few nights ago. And this was the perfect opportunity to let Cas know that Dean had fallen head over heels for him. Without his consent however, Dean’s lips slowly gravitated towards Cas’ and he—

"Ahem."

Dean practically pushed himself out of Cas’s grip, and Cas took a few steps away from Dean for good measure. “Yes Charlie?” Dean sighed. Already missing the warmth of Cas’ hands around his waist.

"Jo is looking for you two." Charlie smiled almost slyly.

"Right ok." Dean straighter his waistcoat and smiled at Charlie, "Where is she?"

Now, Charlie’s smirk was growing more apparent. Dean chose to ignore it rather than start a scene, “Uh.” Charlie mumbled, her eyes snapping mischievously between the two men, “Out by the docks.” Cas took another small step away from Dean.

"Okay…" Dean said slowly. "Thanks Charlie."

If possible, her smirk grew bigger, “No problem.”

The silence hung heavy between the three, and Charlie just kept smiling. Dean wanted to scream at her to stop, it wasn’t like that. However before he could lose it, Cas piped up.

"Dean," Cas said slowly. As if he would spook him if he spoke any faster, "Lets to find her."

Dean could practically feel Charlie’s smirk grow to a full-fledged smile as they walked away.

Dean just hoped that this accident wouldn’t come back to bite him later.

___~•~___ 

It was after two by the time they got back in the states.

“Are you sure you want to go home?” Cas asked, and Dean swore he sounded hopeful. “It’s really late. Sam probably won’t want to be woken up. You can stay at my place if you want.” 

Dean had been home much later than this before. He had come crawling indoors at six am, after Sam was awake and getting ready for school. On these mornings, Dean would fall asleep right on the couch, not bothering to walk to his bedroom. 

But Cas didn’t know that, and Dean wasn’t about to turn down the invitation. He wanted to see Cas’ place, to learn the ins and outs of him through objects laying around on nightstands. He wanted to whisper confessions into his skin in a dark room, so Cas couldn’t see his red face. He knew the feelings were sappy and he tried to push them away, but still the thoughts arose. More than anything, Dean wanted to press his lips to Cas’ again, to feel that head-spinning happiness he’d felt in the car on their first assignment together. 

“Maybe I shouldn’t wake Sam,” Dean managed, his nails digging into the steering wheel as he drove. “Are you sure it’s okay if I stay over? I don’t want to intrude.” 

“Dean-” Cas responded, placing his hand over Dean’s knee. “You’re always welcome to stay with me.”   
And that was all he needed. Dean spun left onto the opposite street and headed in the direction of Cas’ house.

___~•~___

Dean wasn’t sure what he had expected, but Cas’ home was everything he thought it would be. There was a multitude of books strewn about the living room, but otherwise, the place was neat and orderly. His dress shoes were all lined up at the door, and a shelf near the bedroom held even more books. In the corner of the living room was the biggest collection of music Dean had ever seen. Underneath the phonograph was an organized pile of cylinders. More than Dean had seen in stores.

“There’s so much music here,” he commented, migrating towards the machine.

“There’s more in my room,” Cas smiled, gesturing towards the closest door. “I keep my record player in there, but I’m still building that collection.”

“What song is your favorite?” Dean asked, wondering if he knew his own answer to that question. 

“I like Rhapsody in Blue,” Cas responded, dropping his jaw when Dean gave him a confused look. “You’ve never heard that song?” 

Dean shook his head. 

“Well, come on, you have to listen.” Cas led them towards his bedroom. “I only have it on a record. Sorry.” 

Dean followed, sitting on the bed when he reached Cas’ room. His record collection was only slightly smaller than the phonograph cylinders, and held a lot more music that Dean recognized. Cas put “Rhapsody in Blue” on cautiously, careful not to scratch the vinyl. He came and sat next to Dean, maybe closer than he’d intended, but he didn’t move. The two sat silently for a minute, listening intently to the song. 

“You have good taste in music,” Dean noted during a softer section of music. Somehow, their hands had found each other’s and their fingers had interlocked. 

“You have good taste in everything.” 

Dean laughed. “That is the sappiest thing I’ve ever heard,” he told him, though his stomach was filled with butterflies. Dean felt so dumb for liking Cas so much. There was no way in Hell that he deserved a man like Cas. Even for a night. But still, there he was, with his beautiful blue eyes and sex hair, holding onto Dean’s hand like it was a gift. 

“Can I kiss you?” Cas asked, and it was the stupidest question Dean had heard in a while. He leaned in and pressed his lips against Cas’, inhaling sharply in an attempt to take everything in. 

Cas’ lips were chapped, but he was a damn good kisser. His hands trailed Dean’s jacket expertly, unbuttoning and removing both Dean’s shirt and his own. Cas trailed his lips across Dean’s face, onto his chin and down to his neck. 

He held Dean’s body like he’d known it for centuries, trailing his fingers along the freckles on his sides like they were constellations. Dean’s hands trailed the back of Cas’ pants, moving his fingers towards the button as Cas sucked hickeys onto his collarbone.

“Beautiful,” Cas whispered, tracing circles on Dean’s ribcage with his thumb. 

Dean’s head swam as he unbuttoned Cas’ pants. His were removed in a swift motion.

This was nowhere near Dean’s first time. He had been with lots of different people, but none since Lisa, and none like this. Dean wasn’t sure if he had ever wanted anyone as much as this. 

“Is this okay?” He asked, keeping his movements tentative. His fingers were trailing along the waistband of Cas’ underpants as he moved himself downward, pressing their hips together. 

Cas held a hand on Dean’s waist, reaching up to kiss Dean again. “Yes.” He whispered it against Dean’s mouth, following the statement by planting a kiss on the nose. 

With that, Dean was gone. He dropped his hips against Cas’, rubbing against him in desperate motions. It wasn’t a picture-perfect scene, but they would have more time for that later, on different nights, when their bodies knew each other well enough to create perfection in each movement. For now, everything was new, and Dean needed Cas. He needed to hold his body against his own, to shamelessly rock their hips together. 

“Cas,” Dean moaned, embarrassed that he was this close to coming already even though they weren’t naked and they hadn’t gotten much past grinding. The record had long since ended, and the feeling of Cas’ cock against his, even through the fabric, was about to make him come in his pants like a teenager. 

Their speed heightened and Cas began to breathe heavier, emitting little gasps when Dean rubbed against him in the right way. Dean began to stutter as he moaned, reaching the edge as he cherished his movements, keeping his cock against Cas’ for frantic seconds between each rock of his body. 

“Shit, I’m gonna-” Dean cut himself off with a whimper as Cas reached his head up again, propping himself up on his elbows to graze his lips against Dean’s collarbones. 

“It’s okay,” Cas replied, his voice low and rough. “Come for me, Dean.” 

And that was all he needed. Dean was coming in his underwear, his cheeks pink as he began to tremble. Cas followed not a minute later, moaning against Dean’s skin and desperately clutching him at his waist. Dean fell against him, pressing their chests together as he began to kiss Cas’ chapped lips. Even without true contact, it was the best sex Dean had ever had, though he wouldn’t admit it until months later. 

The two rolled around in the sheets for a bit longer, feeling unable to keep their hands off of each other. After what seemed like days of kisses and sucking marks into each other’s skin, they shed their stained clothing. “Please stay,” Cas asked, and Dean responded by laying his head down against the pillow, allowing Cas to curl himself around him, rubbing circles on Dean’s stomach with his thumb as they fell into a quiet rhythm of not-quite-sleeping.

"Dean?" Came Cas' soft whisper against his pulse. 

"Yeah?" He replied quietly. 

"Why are you doing this?" Cas said moving far enough away so that he can look at Dean. 

"Cas, what do you mean?"

"This." He said simply, "This... is so dangerous, it's so... Utterly terrifying. I mean it's the reason my family hates me. I-" he stopped suddenly and darted his eyes away, "Sorry." 

"Hey, hey." Dean reached his hand up to cup Cas' face, "It's alright."

Cas had fallen completely silent, leaning into Dean's touch as if to say to drop the subject. 

But Dean, manly Dean Winchester was cuddling, and since he was already acting out-of-the-norm, of course he wasn't going to let it go.

Pressing a kiss to Cas' forehead, Dean smiled, "Believe me, I know this is dangerous, but I'm willing to risk my life for you if you'd do the same, Cas."

"I would." 

That was the night Dean Wincester began to fall in love.


End file.
